The Road to Tuscany Motorcycle Tour in June 2026 is a 5-day guided tour through Italy’s iconic Tuscany region, featuring rolling hills, cypress-lined roads, medieval villages, and a dedicated wine experience. Designed as an **easy-to-medium riding tour**, it is ideal for couples, two-up riders, and anyone looking for a scenic, relaxed Italian motorcycle adventure.
Embark on an unforgettable motorcycle journey from the heart of the old Roman Empire to the cradle of the Italian Renaissance—a land of exquisite wines, world-class cuisine, and timeless romance (and you’re guaranteed at least two of those treats along the way).
Leaving Rome at once, we’ll dive into the rich history, culture and nature of magical Umbria. From the untamed Apennine wilderness, we’ll ride into the golden hills and cypress-lined roads of Tuscany, where the art of La Dolce Vita takes centre stage. Whether it’s a dip in a thermal bath, a lingering lunch overlooking the countryside, or a cooling scoop of gelato, Tuscany is where life’s simple pleasures become unforgettable. The adventure continues as we venture again south, discovering hidden corners of central Italy before our triumphant return to the Eternal City. A final impressive ride through Rome will lead us to a well-earned celebration and toast to an extraordinary journey.
If you’re looking for an experience without compromises, this is it. Expect superb food and wine, handpicked boutique stays, refreshing pools, impeccable hospitality and much more — all woven into a journey where every turn reveals another reason to fall in love with Italy.
Trip at a Glance
Riding Style: Guided group or Independent (Self-Guided with GPS provided).
Motorcycle: Premium rental (Ducati/BMW/Moto Guzzi) or bring your own bike.
Luggage: Support vehicle included for all participants.
Skill Level: Easy/Intermediate (Long sweeping curves with some tighter hairpins sections).
Tour Highlights
Iconic Tuscany rolling hills and scenic backroads.
Medieval villages and cultural stops.
Dedicated wine experience in Montepulciano.
Comfortable, easy-to-medium route and riding pace.
Perfect for couples and two-up riding.
Who this Tour is For
This tour is ideal for riders who:
Want to explore Tuscany’s famous landscapes and culture.
Prefer easy-to-medium roads suitable for relaxed riding.
Are traveling as couples or in two-up configurations.
Enjoy scenic routes, local food, and wine experiences.
Riding Difficulty & Road Types
Daily distances range from 150 km to 230 km. 4-5 hrs daily riding. 800km total.
Roads include smooth backroads, gentle curves, and minimal traffic.
Overall difficulty: Easy-to-Medium.
Road surface: ~95% asphalt.
Traffic level: Low to medium in town areas.
From Rome via Umbria, to some of the most beautiful Tuscan scenes and life, then back via the Lazio lakes region.
Tour Plan
DAY 1 (18/06) 120 km: ‘WELCOME TO ROME + RIDE TO THE APENNINES’
Airport pickup (12 PM latest) – lunch - motorcycle pickup – tour briefing – sunset ride into the Umbria mountains- traditional dinner in Agriturismo.
DAY 2 (19/06) 220 km: ‘TERNI TO MONTEPULCIANO’
After a hearty breakfast, we’ll set off north west winding through the curvy roads of the Umbrian Apennines. Via charming valleys, hills and medieval villages we’ll reach the striking town of Orvieto, where history, nature and beauty meet in a suggestive way. A lazy lunch in the medieval town, before waving through more rolling hills, passing by Monteleone d’Orvieto and Città delle Pieve, home to the smallest alley of the Italy called Vicolo Baciadonne (Womankissing alley). Crossing into Tuscany via the dreamy landscapes of Valdichiana, we’ll cruise past Chianciano Terme, where Fellini filmed his masterpiece 81/2, before reaching Montepulciano. Here an unforgettable wine tasting experience awaits us. As the sun sets, we’ll toast to the day with exceptional dinner and wines atop this spectacular hilltop town, before settling into our charming historic residence for the night.
DAY 3 (20/06) 190 km: ‘THE GOLD OF TUSCANY’
Starting the day with an authentic Italian cappuccino and croissant while soaking up the idyllic Tuscan countryside, we’ll then glide along the remarkable cypress lined roads this timeless region is so famous for. We’ll traverse the famous Val D’Orcia, home to the celebrated Nobile di Montepulciano and Rosso di Montalcino vineyards, before continuing onto the ‘lunar’ landscape of the Crete Senesi, one of the most suggestive areas of Tuscany, called lunar because of its impressively picturesque bare hills. After lunch and a leisurely stroll in legendary Siena - a celebrated UNESCO World Heritage Site - we’ll ride some more perfect curves before soothing our bodies in the wild and sensational open-air thermal baths of Petriolo. Relaxed and rejuvenated, we’ll ride on to Montalcino, where an authentic Tuscan dinner and a restful night await us at our charming countryside hotel.
DAY 4 (21/06) 233 km: ‘MONTALCINO TO THE ETERNAL CITY’
Ready to embrace our final glorious day in the saddle, we’ll venture further into the breath-taking and mostly unspoilt landscapes of Southern Tuscany’s Maremma, a region still relatively unknown to mass tourism and yet very rich in history and heritage. We’ll ride through forests to the top of Mount Amiata at 1600m, then continue south via incredible towns and roads built into the sheer tuff rock by the Etruscans and Romans. Once in the Lazio region, we’ll stop for a ‘marina vibe’ lunch on Lake Bolsena, before winding down the day onto the gentle roads of the natural reserves of Lago di Vico and Bracciano Martigliano. Finally, we’ll crown our trip with a spectacular sunset ride through Rome where a well-deserved dinner party awaits us.
DAY 5 (22/06): DEPARTURE DAY
Breakfast, return the bikes and head back home, or stay some more days in Rome.
What is included:
4 Days Motorcycle rental.
4 nights hotel & breakfast (Minimum 3*, shared double room).
4 dinners (wine allocation included).
1 Wine tasting experience.
End of tour dinner party.
Airport pickup.
Experienced Italian tour leader (English/Spanish/Italian speaking).
Travel info with GPX / Google maps.
Roadside assistance.
Support vehicle (1 bag per person).
Third party motorcycle insurance.
What is not included:
Fuel.
Lunches.
Entrance fees to optional experiences and sites.
Return transfer to airport.
Alcohol (except for dinner allocation).
Tolls and parking.
Tips.
Flights.
Anything not listed above.
Price options
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Includes roadside assistance and support vehicle for luggage transportation.
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Moto Guzzi Guzzi V7
Aprilia Tuareg
BMW F900R
Yamaha Ténéré
Ducati Scrambler 800
Security deposit €1500
HP extra Insurance excess (damage/ theft €1500)
VIP extra insurance excess (damage €500, theft €1000)
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Ducati Desert X
Hypermotard 950
Ducati Multistrada 950/V2
Honda Africa Twin
Guzzi V85 TT
BMW F900GS
Security deposit €2000
HP extra Insurance excess (damage/ theft €2000)
VIP extra insurance excess (damage €700, theft €1100)
HP extra Insurance excess (damage/ theft €1500)
VIP extra insurance excess (damage €500, theft €1000)
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Moto Guzzi Stelvio
BMW R1250GS
BMW RnineT
Triumph Tiger 1200
KTM 1290s ADV
Ducati Scrambler 1100
Ducati Monster 937
Security deposit €2500
Optional HP Insurance excess (damage/ theft €2500)
Optional VIP insurance excess (damage €800, theft €1250)
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Ducati Multistrada 1150/V4
BMW R1300 GS / RS / RT
Security deposit €2500
HP extra Insurance excess (damage/ theft €2000)
VIP extra insurance excess (damage €700, theft €1100)
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BMW R1300GS Adventure
Security deposit €3000
HP extra Insurance excess (damage/ theft €3000)
VIP extra insurance excess (damage €1250, theft €1500)
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Harley Davidson Electra Glide, Road Glide, Street Glide, Road King, Sport Glide, Heritage.
Motorcycle security deposit without optional insurance €10000.00
Optional basic insurance €20 p/d
(deposit €5000, theft excess €10000, damage excess €5000)
Optional Casko insurance €30 p/d
(deposit €1000, theft excess €3000, damage excess €2500)
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You can select any of these extras on your rider form, after you reserved your place.
Single room supplement €100 p/d
Optional HP insurance €20 p/d
Optional VIP insurance €40 p/d
Modular helmet €5 p/d
Spidi tech jacket €10 p/d
Spidi gloves €3 p/d
GPS €10 p/d
Telephone support €3 p/d
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Start/finish: Rome city (Fiumicino airport is best)
You can follow our tour leader or ride independently with the provided maps.
Minimum number of participants: 8 (If the minimum number is not reached the tour may be cancelled. Then you can switch to self guided or your money will be refunded).
Minor route/hotel changes possible due to conditions.
Comprehensive travel insurance recommended.
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Refundable deposit to secure your place now €800.
You can select bike and any desired extras at the next step.
A receipt with the total will be emailed to you.
The balance is due 60 days before the tour. You will receive a new payment link to settle this.
After booking you will receive an email to complete your Rider Form. Look out for this to enter all your details and preferences like chosen motorcycle, dietary requirements, room upgrade, extra insurance etc.
If you have any questions check our dedicated FAQs page, message us on Whatsapp, or get in touch here:
What Riders Say About This Tour
“It was a once-in-a-lifetime experience, and I can’t wait for the next trip with this amazing team. Highly recommended to anyone who loves motorbikes, great company, and the beauty of Italy! 🇮🇹🏍️” — Armando
“Of all the tour organizers out there, this one is a stand out! Super talented organized operation and local knowledge that made every minute special. A family operation that is professional and committed. I can strongly recommend that you consider their rides. I am back again in 2026 Sardinia!” — Robert
See why riders rate our Tuscan logistics 5 stars on our Reviews page.
FAQ
Q: Is this tour mostly on paved roads or "Strade Bianche" (white gravel)?
A: This is a 95% asphalt tour. We focus on the high-grip, winding secondary roads that showcase Tuscany’s best scenery without the need for off-road experience. 5% will be the access roads to some of the country hotels we stay at.
Q: Can I join the tour with a larger touring bike or a Harley-Davidson?
A: Yes. The "Road to Tuscany" route is designed with flowing curves and wide vistas that are perfectly suited for heavier touring motorcycles and cruisers.
Q: Will we visit specific wineries or historic sites?
A: Our route passes through the heart of Chianti and the Val d'Orcia (UNESCO site). While the focus is riding, we schedule stops in historic borgos for authentic Tuscan lunches, coffee, and a memorable wine tasting experience.
Q: What is the benefit of the "Independent" option for Tuscany?
A: Tuscany is perfect for solo exploration. You can use our pre-loaded GPS to take a detour for a photo or a longer lunch, knowing our support van is moving your luggage to the next boutique hotel.
Guide Bio
This tour is curated by Fabio Affuso, founder of All Routes Italy, combining 20+ years of Italian riding knowledge with a focus on photography-worthy routes and authentic culture. Find out more on our About Page.
View all 2026 motorcycle tours in Italy, or check our rugged Gran Sasso tour.